Hi Cas49, I assume you have tried the two usual methods to update songs, file>update songs or right click your ipod in the source list and update songs.
I have just tried again to update my iPod manually with these four tunes but I got an Error Report "DrWatson Postmortem Debugger".There was a send/don't send message to Microsoft but I did not send.
Any ideas please ?
Hi cas49, i suggest you remove and re install itunes, maybe even browse the help pages at www.apple.com/support as this may a known problem with a remedy